We were caught unawares at how much controversy the question posited this week would generate among MR PORTER’s ranks. As we write this, the office is still sharply delineated into pro- and anti-hoodie camps. One member on the opposing side went as far to say that, unless her date turned out to be Drake in the flesh, she would turn on her heels and leave, never to darken his door – or DMs – again. But for the equally vocal hoodie-on-a-date defenders, the answer is a resounding yes. The real question isn’t “can?”, but “how?”. We’ll get right to it.

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Can I wear a hoodie on my first date?

@adpphotos via Instagram

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First things first, let’s get the basics out of the way: you probably already know it’s advisable to steer clear of anything too baggy, bold or printed with profanities – so it’d be sage to reserve anything from Vetements or Off-White until the third date, at least. We’ll also add – because we can already hear a horde of angry streetwear proponents grumbling in protest – that you shouldn’t be fooled into thinking that a slogan is going to serve as an icebreaker: if the two of you need that much help making small talk, you probably shouldn’t have swiped right in the first place.

To avoid looking like a certain Silicon Valley resident in a hoodie and make a good first impression, the key is to keep it clear and classic. Ground-breaking, right? But playing it sartorially safe is nothing to be sneered at. Nor are garments as downright sophisticated as Massimo Alba’s cashmere-blend pullover, Bottega Veneta’s navy zip-through or, at the sportier end of the scale, Thom Browne’s striped cotton-jersey number. All three are prime for layering under other pieces, which is where there’s scope to elevate the humble hoodie into something else entirely. Depending on where you plan to take your new paramour, you can get away with either a blazer, a bomber or even a denim jacket. Reserve the last option for strictly casual affairs, but if you’ve booked dinner or drinks, an unstructured jacket – we like this throw-on-and-go poplin blazer from Aspesi – will show that you’ve made a decent amount of effort without looking as try-hard as a tailored two-piece might.

As for the rest of your ensemble, proper shoes such as Oxfords and brogues are a big no-no – you’ll run the risk of looking like you’re all work and no play or you’ve just pegged it from the office. Instead, the perfect match is a pair of smart sneakers from the likes of Common Projects or boots from Officine Creative – the latter brand’s Stanfords are a firm favourite and should help you two get off on the right foot. Sorry. We couldn’t help ourselves.